Hydrochloric Acid → HCID 19955533, compound

HRID 440992Notes

Reaction equation

HRID 440992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([I:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Mg].[O:11]=[C:12]([CH3:18])[CH2:13][CH2:14][CH2:15][C:16]#[N:17].Cl>C(OCC)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([I:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH:11][C:12]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=1)([CH3:18])[CH2:13][CH2:14][CH2:15][C:16]#[N:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 764241,3-Dichloro-5-iodobenzeneHCID 82611Hexanenitrile, 5-oxo-HCID 5462224Magnesium

Product 2

HCID 764241,3-Dichloro-5-iodobenzeneHCID 19955533HCID 19955533, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

The Grignard reagent of 3,5-dichlorophenyl iodide was prepared by the reaction of 20.0 grams (0.073 mole) of 3,5-dichlorophenyl iodide and 1.8 grams (0.073 mole) of magnesium turnings in 350 mL of diethyl ether. The reaction mixture was heated at reflux for about three hours and then allowed to cool to ambient temperature. To the Grignard reagent, with stirring, was added dropwise during a 15 minute period a solution of 8.4 mL (0.073 mole) of 5-oxohexanenitrile in 25 mL of diethyl ether. The exothermic reaction caused the reaction mixture temperature to rise to about 30° C. Upon completion of addition, the reaction mixture was stirred for one hour and then was poured into 400 mL of water. The mixture was made acidic with about 80 mL of aqueous 2N hydrochloric acid and extracted with two 200 mL portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chroma-tography on silica gel, using 5% diethyl ether in methylene chloride as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 8.4 grams of 5-hydroxy-5-(3,5-dichlorophenyl)hexanenitrile. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for about three hours
  3. customThe exothermic reaction
  4. customto rise to about 30° C
  5. additionUpon completion of addition
  6. extractionextracted with two 200 mL portions of diethyl ether
  7. dry with materialThe combined extracts were dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure to a residue
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fde881b7d3024d59b23aa95e75b72f57
Source dataset
uspto-grants-1996_05
Patent number
US05521192

Reaction notes

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